In one of our church’s weekly “small group” meetings, we recently discussed Jesus’ encounter with the Samaritan woman at the well, John 4:1-42. It occurred to me that this might be the first non-Jewish convert. My NIV study Bible has a table that puts all four Gospels in single chronological order, and that seems to bear out my hypothesis. What was also interesting is that, not counting disciples and the nameless folks baptized, the very first individual — the one immediately preceding the Samaritan woman — named was Nicodemus. This suggests that Jesus wanted to signal from the get-go that His ministry was universal, including as it did both extremes: On the one hand, a Pharisee and member of the Jewish Council; on the other hand, someone who would be viewed as a sleazy half-breed woman.
In deciding how we ought to go about evangelizing — and of course the Great Commission says we ought to be evangelizing — it makes sense to pay particular attention to those parts of the New Testament that describe how Jesus did it. To be sure, there are things that Jesus said about Himself that we can’t say about ourselves, and there may be other ways in His approach that we cannot adopt wholesale. Nonetheless, in His mixture of bluntness and subtlety, His individualized consideration of who a person was and what the person might most be looking for, and above all in His willingness to reach out to everyone, He presents — unsurprisingly — a great role model.
By the way, given the fact that Jesus Himself reached out to non-Jews, assuming that was known, one wonders why this should have been such heavy lifting for the church when Paul came along. But maybe the issue is better stated as what (old Jewish) rules Gentiles had to follow rather than whether they were welcome at all.